I like Picard's first contact with the Malcorians. The way he made contact, they handled a crisis, he welcomed them into a larger community, but ultimately respected their leader's wishes when they said they weren't ready.

Archer's blunder over a dog has to top the list of worst incidents. Even Janeway left her dang dogs at home and she wasn't the leader of the first human starship in deep space.

I also think there were a lot of incidents in the first season of TNG, where Picard and the crew came off as ineffective weenies in the diplomatic field.

Code of Honor was pretty bad for example, where Lutan kidnapped Tasha Yar and Picard seeming far too accommodating to Lutan after that act. Not to mention Picard's attempts at sabre rattling just come off as pathetic. It seems like in the first season of TNG, the Federation was supposed to bow to every crazy whim the other side had, rather then trying to develop an attitude of mutual respect.

The foreign policy conundrum presented in TNG's "The Wounded" is a fairly fascinating one -- a viewer today could make comparisons to the ongoing issue with Iran's alleged development of nuclear weapons. When should a war be risked to secure from an external threat?

And of course, Star Trek VI: The Undiscovered Country glorifies the diplomatic process.

Code of Honor was pretty bad for example, where Lutan kidnapped Tasha Yar and Picard seeming far too accommodating to Lutan after that act.

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They need the medicine from that world pretty badly, and Lutan did fall from power at the end of the episode through the Enterprise crew's actions, so justice was served to a degree.

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Picard: "... pursuant to Sub-section D-3 I name... the Grizzelas ...

From Ensigns of Command, one of my favorite moments in all the various series.

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Unfortunately they are currently in their hibernation cycle, but they'll awaken in six months, and then we'll get this matter settled. Now, do you want to wait... or give me my three weeks?
He who lives by the rules die by the rules.

That wasn't diplomacy, that was dirty tricks. But it was made necessary by one of the most catastrophic failures of Fed diplomacy: bungling the wormhole situation with the Dominion.

Dominion: don't use the wormhole, the GQ (or at least the part of it the wormhole leads into) is our territory, which we plan to defend with maximum violence.

Feds: STFU, we do as we please. Bring it on, gumbies.

Romulans: WTF, what about us? if the Doms get mad at you, they won't be too selective who they hit. We're blowing up that wormhole before anyone, namely us, gets hurt.

Feds: Those sneaky Rommies! We sure put a stop to their nefarious scheme to protect the Alpha Quadrant.

Romulans, to Cardassians: The Feds are being their usual idiotic selves. This leaves no choice but to handle the situation on our own by a first strike, thus proving that they're not the only idiots around.

...and we all know what happened as a result. The gumbies must have wondered what they did to deserve a quadrant full of Keystone Kops as neighbors.

Worst: We won't develop a cloaking device if you promise not to attack us.

Romulan response: Try to provoke the Federation into a war that makes them look like the good guy.
Real world response: Romulus surrounds Earth with a thousand warships before they even know the war has started.

Worst: We won't develop a cloaking device if you promise not to attack us.

Romulan response: Try to provoke the Federation into a war that makes them look like the good guy.
Real world response: Romulus surrounds Earth with a thousand warships before they even know the war has started.

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True. The Federation Cardassian peace treaty also felt like a huge diplomatic failure, comparable to the Munich Pact. The Cardassians treated that treaty like toilet paper, violated it whenever they wanted to and then used it against the Federation whenever they could. The Cardassians and Federation were at war with each other a few years after the peace treaty was signed.

The Dominion War really was the result of a first-contact gone horribly wrong, IMO.

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To be fair, the Dominion's idea of first contact seems to be conquer a new species, ask questions later.

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And the Federation's response was to sneak a warship into their territory on a mission of cowboy diplomacy. That didn't make the Founders' view of the Federation any better.

That's not to say that the Dominion War was the Federation's fault, but sometimes first contacts don't go well no matter what you do. I'm sure the Dominion wasn't the first new civilization that perceived the Federation as an immediate threat to them and responded with hostility.

True. The Federation Cardassian peace treaty also felt like a huge diplomatic failure, comparable to the Munich Pact. The Cardassians treated that treaty like toilet paper, violated it whenever they wanted to and then used it against the Federation whenever they could. The Cardassians and Federation were at war with each other a few years after the peace treaty was signed.

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Even as a big Cardassian fan, I will say that treaty was horrible. I can't imagine it exactly inspired the Cardassians to respect such weaklings as the Federation showed itself to be. And then the Feddies went and basically sold their own people in the DMZ to curry favor with the Cardassians.

The Cardassians' response to that was basically to take advantage of it.

The Dominion War really was the result of a first-contact gone horribly wrong, IMO.

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To be fair, the Dominion's idea of first contact seems to be conquer a new species, ask questions later.

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And the Federation's response was to sneak a warship into their territory on a mission of cowboy diplomacy. That didn't make the Founders' view of the Federation any better.

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I don't think that anything would've made them view the Federation positively, considering the fact that they've had a few thousand years of circle-linking that reinforced their anti-solid biases. Hell, it took Section 31's bioweapon to bring them to the negotiating table.

Besides, the Dominion killed all those settlers on New Bajor before they kidnapped Sisko and Quark and blew up the Odyssey. All the blame for the war falls squarely on them.

To be fair, the Dominion's idea of first contact seems to be conquer a new species, ask questions later.

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And the Federation's response was to sneak a warship into their territory on a mission of cowboy diplomacy. That didn't make the Founders' view of the Federation any better.

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I don't think that anything would've made them view the Federation positively, considering the fact that they've had a few thousand years of circle-linking that reinforced their anti-solid biases. Hell, it took Section 31's bioweapon to bring them to the negotiating table.

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I think it was actually Odo that finally convinced the Founders that the Federation wasn't a threat--despite the bioweapon--and that was what really ended the war. The cure for the bioweapon was an incentive, but the Dominion did seem prepared to fight to the death without it.

In hindsight, it really seemed more like an issue of time before the Founders were convinced that not all solids were evil and out to get them.

Besides, the Dominion killed all those settlers on New Bajor before they kidnapped Sisko and Quark and blew up the Odyssey. All the blame for the war falls squarely on them.

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Not entirely, because it does take two (or more) to have a war. The Federation had the option from the very beginning of hostilities of destroying the wormhole and sealing off the Gamma Quadrant and further contact with the Dominion. They chose not to.

In a way, the initial contact between the Federation and the Dominion mirrored that a century earlier between the Federation and the Gorn in which the latter perceived the former as invaders and struck a deadly preemptive strike. The main difference is the scale, death toll, and length of time before both sides reached an accord.

And the Federation's response was to sneak a warship into their territory on a mission of cowboy diplomacy. That didn't make the Founders' view of the Federation any better.

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I don't think that anything would've made them view the Federation positively, considering the fact that they've had a few thousand years of circle-linking that reinforced their anti-solid biases. Hell, it took Section 31's bioweapon to bring them to the negotiating table.

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I think it was actually Odo that finally convinced the Founders that the Federation wasn't a threat--despite the bioweapon--and that was what really ended the war. The cure for the bioweapon was an incentive, but the Dominion did seem prepared to fight to the death without it.

In hindsight, it really seemed more like an issue of time before the Founders were convinced that not all solids were evil and out to get them.

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I'm not entirely convinced of that, mostly because the female Changeling linked with Odo in The Search, then with the rest of the Founders and that should've told them that the Federation was no threat. But then they went, "Nah, we're going to impose order on the Alpha Quadrant" to Odo's face. Fast forward a few months and they not only take out a big chunk of the Tal Shiar and practically all of the Obsidian Order, but then follow that up with trying to start a war between the Federation and Tzenkethi. Later, they do succeed at starting wars between the Klingons and Cardassians, then between the Klingons and Federation. So unless we're talking centuries here, I'm not entirely sure the Founders would've changed their minds unless they pushed against the ropes and shown some mercy. The group-think of the Great Link is too strong.

Besides, the Dominion killed all those settlers on New Bajor before they kidnapped Sisko and Quark and blew up the Odyssey. All the blame for the war falls squarely on them.

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Not entirely, because it does take two (or more) to have a war. The Federation had the option from the very beginning of hostilities of destroying the wormhole and sealing off the Gamma Quadrant and further contact with the Dominion. They chose not to.

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Closing off the wormhole would've been a bad move strategically. First off all, doing so would prevent them from gathering intel on the Dominion at a time when they barely knew anything about them. Second, keeping the wormhole open allows the Federation to funnel the Dominion through a known chokepoint instead of worrying 75 years down the line about when and where the Dominion might show up. Third, closing up the wormhole would probably piss off the Bajorans, since their gods live there and their tolerance of Starfleet's presence depends a lot on the fact that DS9's CO is the Emissary. Fourth, it's better to keep the threat immediate and continue the military build up encouraged by the Borg incursions than kick the problem down the road 75 years, when most of Starfleet barely remembers hearing the Dominion in a history class and may not have closed the tech gap with the guys who had guns that went straight through Federation shields.

In a way, the initial contact between the Federation and the Dominion mirrored that a century earlier between the Federation and the Gorn in which the latter perceived the former as invaders and struck a deadly preemptive strike. The main difference is the scale, death toll, and length of time before both sides reached an accord.

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Well yeah, that was because the Gorn were willing to actually negotiate a peace instead of committing multiple acts of galactic scale terrorism and pretending to make peace with people. The Gorn just wanted some land; the Founders wanted to force the entire galaxy into slavery due to their anti-Solid paranoia.